morphine 3-β-D-octylglucuronamide

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: morphine 3-β-D-octylglucuronamide
• 英文别名: (2S,3S,4S,5R,6S)-6-[[(4R,4aR,7S,7aR,12bS)-7-hydroxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl]oxy]-3,4,5-trihydroxy-N-octyloxane-2-carboxamide
• 化学式: C₃₁H₄₄N₂O₈
• 分子量: 572.699
• InChiKey: AFEBUYSLCJJQAB-ZSHRVOPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  141
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  吗啡 在 lithium hydroxide 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 morphine 3-β-D-octylglucuronamide
  参考文献：
  名称：

  A highly toxic morphine-3-glucuronide derivative

  摘要：

  By the coupling of octylamine to the uronic acid function of morphine-3-glucuronide (M3G) a new glycoconjugate (morphine-3-octylglucuronamide, M3GOAM) was prepared. When assayed in both rats and mice up to ng/kg (ip) doses none of the animals survived. The aliphatic octyl chain may be the lethal factor since a closely related derivative (M3GNH2), was not toxic and showed similar opioid antagonist properties than naloxone. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.016

文献信息

• A highly toxic morphine-3-glucuronide derivative
  作者：Mariona Salvatella、Gemma Arsequell、Gregorio Valencia、Raquel E Rodrı́guez

  DOI：10.1016/j.bmcl.2003.12.016

  日期：2004.2

  By the coupling of octylamine to the uronic acid function of morphine-3-glucuronide (M3G) a new glycoconjugate (morphine-3-octylglucuronamide, M3GOAM) was prepared. When assayed in both rats and mice up to ng/kg (ip) doses none of the animals survived. The aliphatic octyl chain may be the lethal factor since a closely related derivative (M3GNH2), was not toxic and showed similar opioid antagonist properties than naloxone. (C) 2004 Elsevier Ltd. All rights reserved.